US3937733A - Salts of iodomethanesulfonic acid with organic bases - Google Patents
Salts of iodomethanesulfonic acid with organic bases Download PDFInfo
- Publication number
- US3937733A US3937733A US05/239,937 US23993772A US3937733A US 3937733 A US3937733 A US 3937733A US 23993772 A US23993772 A US 23993772A US 3937733 A US3937733 A US 3937733A
- Authority
- US
- United States
- Prior art keywords
- salt
- acid
- iodomethanesulfonic
- iodomethanesulfonic acid
- glucamine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 33
- RDFJFVXMRYVOAC-UHFFFAOYSA-N methiodal Chemical class OS(=O)(=O)CI RDFJFVXMRYVOAC-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 229960003695 methiodal Drugs 0.000 title claims abstract description 26
- 150000007530 organic bases Chemical class 0.000 title abstract description 3
- 150000001412 amines Chemical class 0.000 claims description 10
- CUGDYSSBTWBKII-LXGUWJNJSA-N (2r,3r,4r,5s)-6-(dimethylamino)hexane-1,2,3,4,5-pentol Chemical compound CN(C)C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO CUGDYSSBTWBKII-LXGUWJNJSA-N 0.000 claims description 9
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims description 9
- VQSVOQJUFSROBP-LXGUWJNJSA-N (2r,3r,4r,5s)-6-(2-hydroxyethylamino)hexane-1,2,3,4,5-pentol Chemical compound OCCNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO VQSVOQJUFSROBP-LXGUWJNJSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- SNTDZSVLMOLUOX-SGIHWFKDSA-N (2r,3r,4r,5s)-6-(diethylamino)hexane-1,2,3,4,5-pentol Chemical compound CCN(CC)C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO SNTDZSVLMOLUOX-SGIHWFKDSA-N 0.000 claims description 2
- IKXCHOUDIPZROZ-LXGUWJNJSA-N (2r,3r,4r,5s)-6-(ethylamino)hexane-1,2,3,4,5-pentol Chemical compound CCNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO IKXCHOUDIPZROZ-LXGUWJNJSA-N 0.000 claims description 2
- IEQYGSFGZLAWEZ-JQCXWYLXSA-N (2r,3r,4r,5s)-6-[2-hydroxyethyl(methyl)amino]hexane-1,2,3,4,5-pentol Chemical compound OCCN(C)C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO IEQYGSFGZLAWEZ-JQCXWYLXSA-N 0.000 claims description 2
- SSFSWCNUUNPAHB-JQCXWYLXSA-N (2r,3r,4r,5s)-6-[ethyl(methyl)amino]hexane-1,2,3,4,5-pentol Chemical compound CCN(C)C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO SSFSWCNUUNPAHB-JQCXWYLXSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000002872 contrast media Substances 0.000 abstract description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 7
- 229910052740 iodine Inorganic materials 0.000 description 7
- 239000011630 iodine Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 159000000000 sodium salts Chemical class 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 239000012266 salt solution Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229940039231 contrast media Drugs 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 206010002091 Anaesthesia Diseases 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 230000037005 anaesthesia Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002337 glycosamines Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000009608 myelography Methods 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- COCJIVDXXCJXND-UHFFFAOYSA-M sodium;iodomethanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)CI COCJIVDXXCJXND-UHFFFAOYSA-M 0.000 description 2
- GBNXMEVVZBZIAC-SLPGGIOYSA-N (2R,3R,4R,5S)-6-hydrazinylidenehexane-1,2,3,4,5-pentol Chemical compound NN=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO GBNXMEVVZBZIAC-SLPGGIOYSA-N 0.000 description 1
- FQDOAQMGAIINEJ-LJVFLWCUSA-N (2r,3r,4r,5s,6e)-6-hydroxyiminohexane-1,2,3,4,5-pentol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)\C=N\O FQDOAQMGAIINEJ-LJVFLWCUSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 230000010865 X-Ray Contrast Activity Effects 0.000 description 1
- RXDLGFMMQFNVLI-UHFFFAOYSA-N [Na].[Na].[Ca] Chemical compound [Na].[Na].[Ca] RXDLGFMMQFNVLI-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 210000000038 chest Anatomy 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical group OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- RDFJFVXMRYVOAC-UHFFFAOYSA-M iodomethanesulfonate Chemical compound [O-]S(=O)(=O)CI RDFJFVXMRYVOAC-UHFFFAOYSA-M 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000002690 local anesthesia Methods 0.000 description 1
- 210000004705 lumbosacral region Anatomy 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 238000006894 reductive elimination reaction Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 238000002693 spinal anesthesia Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/04—X-ray contrast preparations
- A61K49/0433—X-ray contrast preparations containing an organic halogenated X-ray contrast-enhancing agent
Definitions
- the sodium salt of monoiodomethanesulfonic acid (methiodal sodium) has been utilized for a long period of time.
- this compound has the advantage of being rapidly and entirely resorbable.
- the very low viscosity of compositions comprising this compound makes it possible for the medium to penetrate into the finest fissures and thus render an excellent representation of the details in myelography.
- Disadvantages are the limited representation of the lumbar region and the necessity of prior spinal anesthesia, which constitutes a source of side reactions. According to SCHOBER (Radiopaque Agents and Liquor Space, Springer publishers 1964) a large number of the dangerous complications, such as conditions of shock and collapse, are ascribed to lumbar anesthesia.
- the novel salts of this invention possess such a high compatibility with respect to the neural tissue that a lumbar anesthesia with its associated risks becomes superfluous.
- This essential advantage is attained without a reduction of the favorable properties of the known sodium salt, such as low viscosity and rapid resorption.
- the excellent compatibility of the novel salts permits readily a doubling of the commercially customary concentration of about 100 mg. of iodine per ml. of salt solution to 200 mg. of iodine per ml. of salt solution, whereby the image quality and thus the possibilities of evaluation of the myelographic examination are considerably increased.
- novel salts of this invention are those of monoiodomethanesulfonic acid with glucamine, N-alkyl- and N,N-dialkylglucamines.
- alkyl group contains more than one carbon atom
- the latter two amines can be hydroxy substituted, i.e., N-hydroxyalkyl- and N,N-dihydroxyalkyl glucamines.
- the alkyl portion of the glucamines generally contains not more than 4 carbon atoms, whether it be mono- or dialkyl.
- This invention also relates to novel X-ray contrast agents comprising a novel salt of iodomethane sulfonic acid of this invention.
- this invention relates to a method of X-ray examination, especially lumbar, comprising the administration of an effective amount of a novel X-ray contrast agent of this invention.
- novel salts of iodomethanesulfonic acid of this invention include but are not limited to N-methylglucamine; N,N-dimethylglucamine; N-ethylglucamine; N-methyl,N-ethylglucamine; N,N-diethylglucamine; N- ⁇ -hydroxyethylglucamine; N-methyl,N- ⁇ -hydroxyethylglucamine and N,N-di- ⁇ -hydroxyethylglucamine.
- Glucamine is a known amino sugar alcohol of the formula:
- Glucamine and its N-mono- or N,N-disubstituted derivatives are obtained by reductive amination of glucose with the corresponding amines.
- Glucamine may also be obtained by reduction of glucose-oxime or by reductive cleavage of the N-N-bonding of glucose-hydrazone.
- novel salts are produced by neutralizing the iodomethanesulfonic acid with the selected organic base, up to a pH of 7, or by reacting a glucamine salt with alkali or alkaline earth iodomethanesulfonate.
- This invention furthermore relates to novel X-ray contrast media comprising a novel salt of iodomethanesulfonic acid of this invention and their use in X-ray examination, especially spinal.
- the salts of this invention are formulated, in accordance with their preferred use as X-ray contrast media for myelography, into injectable aqueous solutions.
- novel X-ray contrast agents of this invention can be employed in the same manner as the known sodium salt of iodomethanesulfonic acid, preferably at a higher, e.g., double, the usual concentration.
- a dose of 0.5 ml. of an X-ray contrast agent of this invention having an iodine content of 100 mg. per ml. administered to dogs lumbarly without local anesthesia, shows a good representation of the subdural fissures in the lumbal and thorax zones.
- a 2 ml. dose with a content of 200 mg. of iodine per ml., affords a correspondingly excellent contrast effect and is tolerated without complications or serious side-effects.
- the salts can be administered to all mammals, in amounts effective to yield an X-ray contrast activity, the dosage range to humans being preferably equivalent to about 500 to 2000 mg. of iodine.
- novel compounds of this invention can be administered in the forms customarily employed in pharmaceuticals in admixture with a pharmaceutically acceptable carrier.
- the soluble salts of this invention are preferably employed as an aqueous solution of a concentration preferably between about 30 % by volume and about 80 % by volume and preferably having a pH of about 5-7.
- aqueous solution of sodium iodomethanesulfonate is passed through an ion exchange column in the H + form.
- the arrangement is protected from bright light, since the salt solution is somewhat sensitive to light.
- the acidic main fraction is removed, neutralized with methylglucamine to a pH of 7, and thereafter concentrated to a content of 200 and/or 300 mg. of iodine/ml. Yield: 95% of theory.
- the solution can then be sterilized in accordance with Example 6.
- the acid is liberated from the sodium salt as set forth in Example 1.
- the solution of the acid is neutralized with methylglucamine to a pH of 7, and the neutral solution is concentrated to syrupy consistency.
- ethanol By the addition of ethanol to the syrup, a crystalline product is obtained which is recrystallized from ethanol. Melting point: 93°-94° C. Yield: 91% of theory.
- N,N-dimethylglucamine salt of iodomethanesulfonic acid is obtained analogously to Example 3, m.p. 66°-67° C. (from ethanol). Yield: 87% of theory.
- the glucamine salt solution is prepared in accordance with the above recipe, filled into ampoules or multivials and sterilized at 120° C.
- the solution contains 200 mg. of iodine per ml.
- amines used for preparing the described salts are amino sugar alcohols with the amino function at a different position of the hexitol molecule, e.g. fructamin, galactamin etc.
Landscapes
- Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DT2117014 | 1971-04-02 | ||
| DE19712117014 DE2117014A1 (de) | 1971-04-02 | 1971-04-02 | Salze der Jodmethansulfonsaure mit organischen Basen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3937733A true US3937733A (en) | 1976-02-10 |
Family
ID=5804147
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/239,937 Expired - Lifetime US3937733A (en) | 1971-04-02 | 1972-03-31 | Salts of iodomethanesulfonic acid with organic bases |
Country Status (15)
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5441517A (en) * | 1991-11-08 | 1995-08-15 | Kensey Nash Corporation | Hemostatic puncture closure system and method of use |
| US5676689A (en) * | 1991-11-08 | 1997-10-14 | Kensey Nash Corporation | Hemostatic puncture closure system including vessel location device and method of use |
| US20090005777A1 (en) * | 2001-04-24 | 2009-01-01 | Vascular Closure Systems, Inc. | Arteriotomy closure devices and techniques |
| US20090143808A1 (en) * | 2001-04-24 | 2009-06-04 | Houser Russell A | Guided Tissue Cutting Device, Method of Use and Kits Therefor |
| US20090143789A1 (en) * | 2007-12-03 | 2009-06-04 | Houser Russell A | Vascular closure devices, systems, and methods of use |
| US8992567B1 (en) | 2001-04-24 | 2015-03-31 | Cardiovascular Technologies Inc. | Compressible, deformable, or deflectable tissue closure devices and method of manufacture |
| US9345460B2 (en) | 2001-04-24 | 2016-05-24 | Cardiovascular Technologies, Inc. | Tissue closure devices, device and systems for delivery, kits and methods therefor |
| US11522302B2 (en) | 2017-08-04 | 2022-12-06 | Tdk Electronics Ag | Connection of a connection wire and a connection element |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB353477A (en) * | 1930-04-24 | 1931-07-24 | Ig Farbenindustrie Ag | Process for the manufacture of iodo methane sulphonic acid and salts thereof |
| FR708270A (fr) * | 1930-12-23 | 1931-07-22 | Ig Farbenindustrie Ag | Production d'acide iodeméthanesulfonique ou de ses homologues |
-
1971
- 1971-04-02 DE DE19712117014 patent/DE2117014A1/de active Pending
-
1972
- 1972-03-16 IL IL39005A patent/IL39005A/en unknown
- 1972-03-21 DK DK132572A patent/DK131934C/da active
- 1972-03-22 CH CH425972A patent/CH579031A5/xx not_active IP Right Cessation
- 1972-03-24 NO NO998/72A patent/NO135181C/no unknown
- 1972-03-27 GB GB1416372A patent/GB1387175A/en not_active Expired
- 1972-03-29 SE SE7204128A patent/SE391519B/xx unknown
- 1972-03-30 ZA ZA722184A patent/ZA722184B/xx unknown
- 1972-03-30 AU AU40634/72A patent/AU467239B2/en not_active Expired
- 1972-03-30 AT AT279072A patent/AT312795B/de not_active IP Right Cessation
- 1972-03-30 CA CA138,655A patent/CA999880A/en not_active Expired
- 1972-03-30 AT AT250573A patent/AT323121B/de not_active IP Right Cessation
- 1972-03-31 US US05/239,937 patent/US3937733A/en not_active Expired - Lifetime
- 1972-03-31 FR FR7211559A patent/FR2132352B1/fr not_active Expired
- 1972-03-31 BE BE781587A patent/BE781587A/xx unknown
- 1972-04-04 NL NL7204492A patent/NL7204492A/xx unknown
Non-Patent Citations (2)
| Title |
|---|
| Hilal, Investigative Radiology, Vol. 5, pp. 458-468 (1970). * |
| stecher et al., The Merck Index (8th Ed.), Merck & Co., Inc. Rahway N.J. p. 674 (1968). * |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5441517A (en) * | 1991-11-08 | 1995-08-15 | Kensey Nash Corporation | Hemostatic puncture closure system and method of use |
| US5676689A (en) * | 1991-11-08 | 1997-10-14 | Kensey Nash Corporation | Hemostatic puncture closure system including vessel location device and method of use |
| US6090130A (en) * | 1991-11-08 | 2000-07-18 | Kensey Nash Corporation | Hemostatic puncture closure system including blood vessel locator and method of use |
| US20090005777A1 (en) * | 2001-04-24 | 2009-01-01 | Vascular Closure Systems, Inc. | Arteriotomy closure devices and techniques |
| US20090143808A1 (en) * | 2001-04-24 | 2009-06-04 | Houser Russell A | Guided Tissue Cutting Device, Method of Use and Kits Therefor |
| US8518063B2 (en) | 2001-04-24 | 2013-08-27 | Russell A. Houser | Arteriotomy closure devices and techniques |
| US8992567B1 (en) | 2001-04-24 | 2015-03-31 | Cardiovascular Technologies Inc. | Compressible, deformable, or deflectable tissue closure devices and method of manufacture |
| US9345460B2 (en) | 2001-04-24 | 2016-05-24 | Cardiovascular Technologies, Inc. | Tissue closure devices, device and systems for delivery, kits and methods therefor |
| US20090143789A1 (en) * | 2007-12-03 | 2009-06-04 | Houser Russell A | Vascular closure devices, systems, and methods of use |
| US8961541B2 (en) | 2007-12-03 | 2015-02-24 | Cardio Vascular Technologies Inc. | Vascular closure devices, systems, and methods of use |
| US11522302B2 (en) | 2017-08-04 | 2022-12-06 | Tdk Electronics Ag | Connection of a connection wire and a connection element |
Also Published As
| Publication number | Publication date |
|---|---|
| IL39005A0 (en) | 1972-05-30 |
| FR2132352B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-04-25 |
| AU467239B2 (en) | 1973-10-04 |
| DE2117014A1 (de) | 1972-10-26 |
| GB1387175A (en) | 1975-03-12 |
| BE781587A (fr) | 1972-10-02 |
| FR2132352A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-11-17 |
| NL7204492A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-10-04 |
| NO135181B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-11-15 |
| ZA722184B (en) | 1972-12-27 |
| DK131934C (da) | 1976-03-22 |
| AT312795B (de) | 1974-01-25 |
| AU4063472A (en) | 1973-10-04 |
| AT323121B (de) | 1975-06-25 |
| SE391519B (sv) | 1977-02-21 |
| NO135181C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-02-23 |
| CH579031A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-08-31 |
| DK131934B (da) | 1975-09-29 |
| IL39005A (en) | 1974-12-31 |
| CA999880A (en) | 1976-11-16 |
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